New water-insoluble azo dyestuffs



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l atented Nov. 24, 1931 TUNITED STATES PATENT OFFICE EUGEN GLIETENBERG, OF LEVERKUSEN-ON-THE-RHINE, GERMANY, ASSIGNOR TO GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OI DELA- WARE NEW WATERINSOLUBLE AZO DYESTUFFS No Drawing. Application filed January 19, 1928, Serial No. 248,012, and in Germany January 25, 1927.

The present invention concerns new wa- The following examples will illustrate my ter-insoluble azo dyestuffs. They have most invention: probably the general formula: Ewample 1.Cotton which has been impregnated with a solution of grams of 2: 3- a 5 OH f NH R3 hydroxynaphthoic acid a-naphthalide per OH? litre is developed in the known manner with a solution containing 2, 4 grams of diazotized N benzoylamino-as-meta-xylidine of the for- R1/ Rz mula. 10 wherein R represents hydrogen alkyl, ar- NH! alkyl R a benzoylor substituted benzoylgroup, and R an aromatic nucleus which may be substituted by any substituent, e. g. an 1 alkyl, an alkoxy, the nitro group or halogen, l none of these substituents being a hydroXy-, 0B1

sulfoor carboxylic acid group.

My new dyestuffs are prepared in substance or on the fibre by combining the arylides of g the 2:3-hydroxynaphthoic acid with the di ma/mph 2. C0ttOn.Wh1ch has been 5y t azo compounds of such asymmetric meta pregnated a Solutlon of 4 grams 9 Xylidines, as have another amino group in naphthylilmlcle of 2:3'hydrOXynaphthole the meta position to the Xylidine amino group 301d H litre 13 d p d the known in which one of the hydrogen atoms may be t a sohmon cqntammg 4 ai f 0 replaced by alkylor aralkylgroup and dmzo tlzed benzoyklmmofls'nteta'xyhdme of I the other hydrogen is substituted byabenzoyl the formula mfntloned Example 1 a It or Substituted benzoyl group soaped. A bluish-red dyeing of exceeding In accordance with the invention azo dyefaslgness to kler bolhng 1 stuffs are obtained, which are distinguished mample ig has been by outstanding fastness to light and kier prilgnated Wlth gtsolution 0 grams 3 7:?" boiling dyeing cotton especially clear shades, hy r9xynilphtholc acldf5'chloro'QTtOhUdKEQ similar to alizarine red. The color lakes preper iltre developed Wlth a solutmn pared from them are distinguished by full azotlzed f of methyl'benzoyl'ammo' bluish-red shades of exceeding clearness and as'metwxyhdme of the formula: fastness to light. NHQ

In their dry pulverized form they are generally red powders insoluble in water, soluble H in sulfuric acid with a bluish-red coloration on; and yielding upon reduction with stannous OH5.CO N do chloride and hydrochloric acid a substituted Cm meta-Xylidine of the general formula:

and worked up in the known manner. A

| bluish-red dyeing is produced. OH3 Err-ample 4.When 3 grams of dichloroand soaped. A bluish red dyeing is thus ob- 1 benzoyl-amino as-meta-xylidine of the forr R: mula:

l CH3 CH; Cl

wherein R1 and R2 mean the same substitu- H C O O a N- 00- -01 cuts as mentioned above and an arylide of i anl-amino-Q:S-hydroxy-naphthom acld.

per litre are taken instead of methylbenzoyl amino Xylidine of Example 3, a more yellow bluish red dyeing in obtained than in EX- amples 1 and 2.

I claim:

1. As new products the mono-azo-dyestuffs of the general formula:

one on 10-Nana wherein R represents hydrogem'alkyl, benwherein R and R mean the same substituents as mentioned above and an arylide of an 1-a1nino-2.3-hydroXy-naphthoic acid, dy-

ing cotton bluish red shades being distinguished by outstanding fastness to light. 7

2. As a new product the mono-azo-dyestuff of the formula:

being in its dry pulverized form a red powder, insoluble in water, soluble in sulfuric acid with a bluish-red coloration, yielding upon reduction with stannous'chloride and hydrochloric acid 1-amino-2-hydroxy-3- naphthoic acid-,B-naphthalide and benzoylamino-as-meta-Xylidine, dyeing cotton clear bluish-red shades of good fastness to light and kier boiling. V V V 3. As new products of manufacture material dyed clear bluish-red shades of good fastness to light and kier boiling with a dyestuff as claimed in claim 1. i p 3 I 4c. As new products of manufacture material dyed clear bluish red shades of good fastness to light and kier boiling with the dyestuff of the probale formula: V

(EH3 (F O NH IIIH $0 C 115 In testimony whereof I have hereunto set my hand. 7

i EUGEN GLIETENBERG. 

